


Rules Are Meant To Be Broken

by queer_and_longing



Series: Sanders Sides Smut One Shots [19]
Category: Sanders Sides (Web Series)
Genre: Accidental Choking, Anal Sex, Car Sex, Choking Kink, Established Logic | Logan Sanders/Morality | Patton Sanders, Established Remus Sanders/Virgil Sanders/Janus Sanders, Female terminology used to describe a trans man's genitals, High School AU, Implied shower sex, M/M, Thomas is 24, Trans Male Character, Trans Roman, Vaginal Fingering, Vaginal Sex, age gap, implied fletching, trans Logan, trans author, underage bc Roman is interpreted as 17 almost 18
Language: English
Status: Completed
Published: 2020-06-01
Updated: 2020-06-01
Packaged: 2021-03-02 22:35:07
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,979
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24494356
Author URL: https://archiveofourown.org/users/queer_and_longing/pseuds/queer_and_longing
Summary: Inspired from @sanderssidessmutprompts #709 and #692. Neither perfectly fit for this fic, but they were the inspiration behind this.709: Roman is an average student, not bad grades but good at his extracurricular stuff, except he gets bullied for his sexuality. He takes comfort in talking to the openly gay teacher, Thomas, and maybe things go a little further than friendly comforting.692: Roman is transgender and insecure about it, nobody knows about it, especially not Thomas. But he confides in Thomas when he gets a little frisky with Roman only to be devastated when he thinks Roman is shutting him down instead of for the real reasons.
Relationships: Creativity | Roman "Princey" Sanders/Thomas Sanders
Series: Sanders Sides Smut One Shots [19]
Series URL: https://archiveofourown.org/series/1225250
Comments: 14
Kudos: 45





	Rules Are Meant To Be Broken

**Author's Note:**

  * For [PastelBlueLuna](https://archiveofourown.org/users/PastelBlueLuna/gifts).



Senior year of high school was supposed to be happy and fun, but here Roman was silently crying while he attempts to do the in class math homework Mr. Sanders assigned. Roman was getting teased for being gay ever since he accidentally sat his phone down with grindr still pulled up on it. It wasn't in Mr. Sanders class, thank god! It was always in his class prior to Mr. Sanders.

Roman usually sat alone in the back of the classroom, he wasn't too good at math anyway, he didn't need someone to make fun of him for being stupid too. Roman wiped another tear that fell down his face, and looked at the results on the latest quiz Mr. Sanders was handing back. His breath got shaky as he saw that 42% circled in red ink and a "see me after class" note next to it. Mr. Sanders is cute, so he's always been striving to impress him, even if this is his worst subject.

Forty-five minutes later, the professor dismisses them. Roman, still red faced and puffy eyes, walks up to Mr. Thomas like a new born baby deer. "Roman," he takes a serious look at him and raises his eyebrows, he hesitates, "come to my office with me, please." Mr. Sanders' body language indicating that wasn't the plan, but it is now.

Roman walks with Mr. Sanders arms wrapped around his middle, looking like he is struggling to breathe. Thomas waits patiently until he and Roman can get an empty elevator. Once he gets to his office, Roman hesitantly sits down.

Mr. Sanders sighs, "Roman, I wanted to talk to you about getting you a tutor," he pauses and looks at Roman who is refusing to make eye contact and sighs again, he sits down next to Roman who tenses a little, "Can I touch you?" He sticks he hand out palm up, Roman nods his head in an affirming gesture and places one hand on Mr. Sanders.

Mr. Sanders shifts his hand so his thumb is straddling Roman's, he starts rubbing his thumb in a soothing manner. "Now, Roman," Roman meets his very kind eyes, "can you tell me what's been going on?" 

Roman stiffens on the couch as anticipated. Thomas continues to rub Roman's thumb. Roman forces his gaze back to Mr. Sanders. He softly sniffles, but it's already caught by Mr. Sanders. "It's nothing." Mr. Sanders gives him a hard look up and down. "It's not nothing, Roman. I've noticed that you come out of the room looking puffy eyed and a wreck for a week. It's something big enough to move you to tears." Roman just listens and wipes his face some more. "Roman, I know I have no right, but I am worried about you and I would like to hear what's going on in your head."

Roman takes his hand back from Mr. Sanders', he takes a deep breath. He mumbles out a sentence, that Mr. Sanders doesn't quite catch. "What was that Roman? I couldn't hear-" "I'm being bullied for being gay," Roman damn near shouts. He starts to stand up and walk away, "I'm sorry Mr.-" "You can call me Thomas." Roman freezes in his tracks and looks back at Mr. S- Thomas. "I'm gay too. If that helps." Thomas grins sheepishly. Roman sits back down next to him.

"Listen, I know I'm not supposed to do this," he looks at Roman in the eyes and smiles, "would you like to go on a date?" Roman looks at him with his mouth open. "Are you sure? I'm not like a normal guy" Thomas cocks his head, "What do you mean?" Roman takes an audibly loud gulp. "I'm transgender." "Oh," Thomas smiles, "Is that all?" Roman makes eye contact with him and nods a little shocked. "Then yeah, I'd still like to take you on a date. But I still want to recommend a tutor." Roman laughs. "Do you know Logan Berry-Hart?" Roman turns red, "He's my best friend." Thomas laughs, "Talk to your friend." Roman smiles as he turns to walk out. "Roman?" He turns back around. "8 o'clock?" Roman nods.

~~~

"That's a horrible idea!" Patton wails. Virgil has his hand covering his mouth trying not to laugh while covering his face in Remus' shoulder.

"Why not?!" Roman already has his sparkly eyeshadow on, red crop top with a gold crown on it, tight black skirt that made his booty pop, and stilettos so sparkly they could rival Dorthy's red slippers.

"I think it's a great opportunity!" Remus exclaimed "I mean no one has wanted to date my brother since he came out and started transitioning. I mean we look exactly the same now, and yet no action." Remus shakes his head. "It's a damn shame."

"Just because you're in a throuple, doesn't mean you can be rude. Now, too much?" Roman gave a twirl. "Now at all, but I would've gone sluttier." "Psh. Don't remind me." Roman turned to start putting on his red single gem earring that stayed close to his ears. You know, just incase things get wild, don't want loose jewelry.

Logan had to be the voice of reason since a) Patton can be an over protective dad (even though he's not related to Roman), b) Remus wasn't going to talk him out of it and neither were Virgil and Janus since they both started dating Remus under some strange ass circumstances they still won't tell him about, and c) Roman really only listened to dating advice from Logan (not to mention Logan is transgender himself and somehow got Patton to date him). "Roman," he turned fasting the last earring and humming questionably, "what is your intention? Please don't tell me you want to sleep with him to get a better grade in the class."

"Oh god no." Everyone in the room looked confused and surprised, Roman shrugged and picked a lip stick color. "In fact he told me to have you help me out and tutor me in the class, Specs." Roman puckered his lips and put the finishing product on his lips. "Now, if you'll excuse me." The click of heels past them and out the door was the last they seen of Roman that night.

~~~

Well, the dinner went pretty alright. Well better than alright. Roman looked up to Thomas from beneath his bangs, Thomas's hard cock swallowed down his throat, lipstick staining his shaft. Roman slipped his eyes shut as Thomas' hands gently rested on his cheeks. Honestly, having Thomas fuck his throat has made him the wettest he's ever been in his life. Well, besides when Thomas hand crept up into Roman's pants at dinner and Roman let him finger him as they waited for the check. Roman's little cock jumping at every noise, and honestly hasn't stopped since. Thomas continuing to finger and tease him as he drove back to his house, Thomas eating him out until he cums while parked inside the garage, and carrying Roman to his bedroom blindly kissing and marking him up the whole time. It's the best sex Roman has had in his life, and it's no where near over.

Roman doesn't realize how sore his throat has become until Thomas pulls him off his cock earning a reluctant whine and glassy eyes from Roman. "For a virgin," he smiles darkly at his sub, "you're very talented." He bends down to capture Roman's lips and move him back to his feet and push him gently down on the bed. Roman is still wearing every bit of clothing he wore on the date, except his panties that have long been forgotten. He thanks god that he didn't wear his binder today as Thomas pushes the material of his shirt up to expose his breasts and Thomas licks and sucks on one and kneads the other. Roman gasps as Thomas' cock ruts against his exposed pussy, tiny cock twitching. He doesn't even care if Thomas decides to fuck him with his clothes on, he just needs that thick length in him like yesterday.

Roman is quite literally melting into his bed as Thomas continues to rut against his cock and switching his menstruations to lick and knead his other breast, heels digging into his lower back. Roman's a little surprised as he suddenly cums on the upstroke of Thomas's cock. He whimpers. Thomas looks down to see a dripping pussy and Roman's hole clenching and unclenching around nothing, looking terribly empty.

He reaches up to rub a hand through Roman's hair and capture his lips sweetly. "I'm gonna fuck you now, ok?" "Ok," Roman whispers, voice heavenly soft. He rubs the head of his cock near the entrance and softly pushes in. Roman gasps so loud Thomas though he's hurt him and pulls out. "I'm ok." He looks into Thomas' eyes, "A little different than having it in your mouth." He laughs and Thomas smiles. "Just relax ok? I'll take care of you." Roman slips his eyes shut again and gets lost in the feeling of Thomas shoving every thick inch inside him until he feels his hips flushed with his own. Roman hums and finally remembers to breathe.

Thomas goes back to sucking, licking, and kneading his breasts as he fucks him slowly at first and speeding up ever so often to have him slamming his cock into Roman's obscenely loud and squelching pussy. Roman's breathing so loud and heavy with every moan ripping out of his throat without a care. Pussy clenching tightly on Thomas' cock making him near his edge sooner than he'd like. Roman squirting around his cock as Thomas doesn't get a change to pull out and cums inside of him. They lay like that for a good while catching their breath, Roman running his hands through Thomas' hair and down his back muscles. He can feel Thomas twitch inside him as his cock reluctantly tries to get hard again. He thinks he feels either his own cum or Thomas' dribble down his hole.

While Thomas can breath again he shoots up like a rocket and looks Roman in the eye. He looks so shameful as he says, "I'm sorry I came in you." Roman pouted for a second reaching up to Thomas' face and stroking his face with his thumb. He chuckled a little. "It's ok. But can you do me a favor?" Thomas smiled a little, "Sure." Roman's voice went down an octave, "Since you want to make a fucking mess," Thomas's breath caught, "a good boy would let me sit on his face and eat it out of me." Thomas frantically nodded. Roman added, "And maybe I'll reward him by sucking it off his slick cock." "Mmm. Please."

Then suddenly the roles were reversed. Roman loved the feeling of getting the cum eaten out of him as he licked and sucked off every inch of Thomas' cock. He was starting to find the taste of cum addicting. He gasped as he felt a wondering tongue travel from his spit slick hole to his asshole. It felt weird but very pleasurable as he worked the tight ring on muscle open. Roman lay panting near Thomas' cock still idly stroking it, fully hard at this point. Roman lost himself in the pleasure as Thomas pushing two lubbed fingers in in ass, tongue licking lightly at his rim. He doesn't remember hearing the cap open, but grateful that he's thinking about lube. Roman got lost before he was made aware that he had four fingers in his ass, Thomas twitching in his hand as he asks Roman if he can fuck his ass. Who's Roman to deny a polite man.

Thomas fucked him from behind frantically, hand tighting around Roman's throat. Being fucked in the ass has already made his body super sensitive, but the tight hand on his throat has made him zero in to that feeling. Roman wasn't even thinking of his own pleasure anymore, he want thinking about his dysphoric body, he let his breasts bounce with every hard slap of cock into his body, pussy dripping, tiny cock hard and twitching, and body violently shaking as he looses to fight to gather more air. He feels Thomas cum in him and at the same time let's go of his throat. Roman is coughing violently as Thomas shoves a butt plug into him. 

He moves to be in Roman's line of blacking sight. "Hey, Roman, can you hear me." Roman can't stop coughing long enough to answer, instead he gives a thumbs up and sits down. "Breathe with me ok? In for 4, hold for 7, and out 8." He puts Roman's hand on his chest. "Just close your eyes and focus on the feeling, ok?" It takes almost thirty minutes from Roman to complete a full cycle, and nearly an hour for Roman to breath calmly. "Hey, you ok?" Roman nods, "Just sleepy," he says in a small child like voice, "can we cuddle?" He looks almost weepy as he gives puppy eyes to Thomas. "Yeah. Lay down. I'll get something to wipe you down with." He comes back and makes Roman take two pain pills and drink a full glass of water as he works to quickly wipe him down. Roman lets Thomas curl around him hugging him to his chest. He kisses the back of his head.

Roman wakes up startled as he recognizes that he's naked and trapped in some man's arms. He turns around to see Thomas's peaceful sleeping face before he realizes what happened last night. He wiggles out of his grip and heads to the bathroom to pee. He gets done and washes his hands and nearly screams at the finger prints that run the length of his neck. There's no down playing what happened to his friends and brother. Jesus Christ. "Roman?" He jumps a foot in the air. He turns around to see Thomas in the doorway. Thomas walks over to him and gently examines his neck. "I'm so sorry." He whispers, face falling as he touches a red spot and Roman hisses.

Roman laughs, "Would it make you feel better to say that I liked it?" Thomas face looks torn, Roman tried to back peddle. "Although next time, let's try to research breath play and have safe words and stuff. Ok?" Thomas' face doesn't change. "You'd still like to do stuff with me?" Roman softens, "Yeah. I'm glad you took my virginity." Thomas pulls him into a hug. "I'm still so sorry." He sounds like he might start crying. Roman holds him tightly.

When Roman feels like Thomas has caught his breath and feels calm in his arms, he has a question that absolutely needs answered. "So, I assume I'm still full of cum and stretched out with this butt plug. What were you planning on doing?" Thomas lets out a deep sigh, "I was gonna eat it out of you," he says in a small voice and pushes himself out of Roman's grip to look him in the eye. He touches the bruises littering his neck, "But I almost killed you, so I can just clean you up if you want." Thomas runs his fingers down Roman's neck waiting for his answer looking more and more like a lost puppy.

Roman quirked his lip up, "You know I have a better idea," Thomas looked back up at him, "you can eat me out in the shower. How does that sound?" Roman hooked his finger underneath Thomas' chin. Thomas blushed and nodded his head, Roman smiled and kissed him. He pulled Thomas towards the bathroom by his hands, "Come on my little prince."

~~~

Roman seriously contemplated covering up the bruises around his neck. They weren't too bad considering they weren't that deep when they first formed and he did have a three day weekend to let them heal. His parents looked seriously concerned when he came home with them, but didn't talk about it. Remus made fun of him for it at any chance he got staying that "he didn't know Roman had a choking kink, but was glad he got laid." He kept looking at them in the mirror of his locker and grimaced at them. They're healing a lot quicker than he thought, but now they've turned an ugly brown and yellow color.

Roman's friends were approaching with Remus who had a shit eating grin on his face. "Roman!" Janus yelled. Roman shut his locker door as the five of them walked closer to him. Patton basically bouncing with each step holding Logan's hand tightly forcing his arm to bounce with him, Remus holding Virgil's and Janus' hands while whispering no doubt about why Roman looks like someone choked him in a fight to Janus who looks confused and relieved.

Patton squealed when he got in a better ear shot of Roman without having to yell at him. "How'd the date go?" The other four looking at him inquisitively, "it was really good," he said as his face flushed as his cheeks flushed a royal red color. "You think there'll be a second date," Virgil asked as he smirked with an all knowing smirk. Bastard. "I don't know... maybe... I hope so." Logan reaches out to touch Roman's hand and smiled, "We're proud of you buddy." Roman smiled as the bell rang. "Come on or we'll be late."

Roman felt really good. Little did his friends know that Roman would for sure have a second date. It'll be in a few weeks after they graduate. Roman didn't want Thomas to get in trouble with the school board, he's already broken a few rules on that one night alone, but they're free to do whatever they want after he crosses that stage and gets his diploma. He can't wait to get his hands on him again.

**Author's Note:**

> Please leave comments 🥺❤️


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